Why Your Digital Transformation Might Be Missing The Point

The push toward AI and digital transformation is accelerating, but so are the growing pains.

Recently, Microsoft announced the retrenchment of 6,000 employees, including an AI Director. While AI continues to be a major focus for the company, the move sparked wider conversations about the complexity of leading transformation, especially when workforce shifts and evolving priorities are involved.

It reflects a broader challenge many organizations face: how to balance ambitious transformation goals with the real impact those changes have on people, whose engagement and readiness directly shape business outcomes.

Digital transformation cannot succeed on ambition alone. Employees are often told they’re part of an exciting new chapter, only to encounter layoffs, role ambiguity, or unclear priorities. When what they hear doesn’t match what they experience, trust erodes. And without trust, momentum fades.

Purpose must come first. Then clear actions and communication must follow. And most importantly, people must be included in both the thinking and the journey.

The most successful digital transformations are not just about technology. They are anchored in clarity, guided by intention, and shaped with the human experience at the center.

Are We Solving a Problem or Following a Trend?

In a recent conversation, a CTO of a global organization joked that their company is pursuing so many AI initiatives that it would “bring world peace and solve global hunger” very soon. It was tongue-in-cheek, but not far from the reality many organizations face. AI and digital transformation are too often treated like the latest trend, adopted out of fear of missing out rather than intention.

In many organizations, the pressure to move quickly on AI and digital transformation is intense. Teams generate long lists of tools and initiatives, hoping to find the spark that drives meaningful change. With boardrooms under increasing scrutiny to show progress, transformation can unintentionally become a checkbox exercise. Tools may be rolled out not because they solve a clearly defined business challenge, but because they look good on a slide deck. Teams are tasked with delivering innovation fast, but often without a shared understanding of what problem they’re solving or why it matters to them. The conversation quickly shifts to productivity, efficiency, and performance metrics without clear communication on how these changes support people or customers besides the fact that the leaders is looking at these data closely now. 

The result? At best, confusion. At worst, misalignment, resistance, and stalled performance that jeopardizes transformation goals.

What is missing? The clarity of purpose.

From Buzzwords to Purpose: Driving Intentional Change

Often when I ask leaders why they want to implement AI, the answers are:

“It is a strategic initiative.”

“It will help us stay competitive.”

“Our competitors are doing it.”

In today’s hyper-competitive landscape, AI and digital transformation have become buzzwords and line items on every boardroom agenda. Too often, transformation efforts are driven by industry pressure or fear of being left behind. Businesses rush to adopt AI, automation, or new technologies simply because everyone is doing so. The result is change initiatives that are reactive, not strategic; imitative, not intentional.

Real transformation does not begin with technology. It begins with clarity of purpose. Strategy without clarity creates noise. If your transformation lacks a defined purpose that your people understand and believe in, it risks becoming just a box-ticking exercise.

Before asking “Which tools should we implement?” we should first ask:

• Why are we transforming in the first place?

• Who is this change for? (Hint: not the highest ranking person in the room)

• What measurable outcome are we hoping to achieve for our people, customers, and business?

Transformation without clear intention is like setting sail without a compass. You may be moving fast, but not necessarily in the direction that serves your business or your people.

Intentional transformation is different. It is grounded in purpose, aligned to strategic goals, and designed with the human experience in mind. It ensures that technology adoption solves real problems, not just follows trends. It creates momentum, not resistance. And most importantly, it earns the trust and engagement of your people, which is the only real engine for sustainable change.

A Simpler and More Human Approach

I recently reconnected with Dr. Tan Hong Ming, Deputy Head at NUS Business School and senior lecturer of the AI for Leaders executive program, and our conversation was a simple yet powerful reminder that digital transformation does not have to start with technology. It starts with people. His approach was refreshingly straightforward:

“Ask your employees which tasks take the most time or cause the most frustration. Understand their process. Help them improve it. If the solution involves AI, great. If not, that is okay too.”

This framing makes all the difference. Transformation is no longer something done to employees. It becomes something done with them, rooted in real needs, not buzzwords.

It reminded me of one of my favorite books, Start with Why by Simon Sinek. In it, Sinek argues that people are inspired not by what a company does, or how it does it, but by why it does it. The most trusted and successful organizations lead with purpose. They make decisions based on a clear and compelling reason that resonates with both their people and their customers.

The same principle holds true for digital transformation. The “why” behind transformation is not the technology itself. AI is just a tool and tools evolve. But what doesn’t change is the need to solve meaningful problems, improve how people work, and unlock better outcomes for teams and customers.

When organizations fail to articulate why they are transforming, what problems they are solving, whose lives they are improving, and what value they hope to create, transformation feels hollow. Employees become disengaged. Resistance grows. The change feels like it’s being imposed, rather than co-created.

But when transformation starts with why, it becomes magnetic. It invites buy-in. It gives people a reason to care, a reason to participate, and a reason to trust the process. Purpose becomes the anchor that keeps the entire journey focused and human-centered.

Whether you're launching AI initiatives, redesigning operating models, or driving large-scale workforce transformation, the first question shouldn’t be what should we do? or how fast can we move? The first question should be: Why are we doing this?

The People Gap in AI Transformation

Clarity of purpose is the starting point, but it’s not enough on its own. As AI adoption and digital transformation are accelerating across industries, so is employee uncertainty. Many are left questioning what these changes truly mean for their future as organizations restructure and redefine roles, especially when job reductions include roles tied to innovation itself. This uncertainty goes beyond confusion. It erodes trust, weakens psychological safety, and risks derailing even the most well-planned transformation efforts. People need more than surface-level reassurance. They need clarity, transparency and consistency to build trust, and a clear understanding of how transformation impacts them personally.

To build genuine trust, organizations must create space for honest dialogue about what AI and digital transformation mean for their people. Employees want to know how their roles will evolve, what skills they will need to succeed, and how their career paths will grow as a result. They need to see how this transformation enhances their relevance, not threatens it.

That means going beyond vague commitments and truly taking tangible steps. Leaders need to engage employees in conversations about their development and outline specific actions the company will take to support them. This includes offering training that aligns with emerging business needs, creating new career pathways shaped by technology, and providing mentorship to help employees adapt and thrive with the transformation.

When employees see that digital transformation is being designed with their growth in mind, they are far more likely to embrace the change. AI should not feel like something is happening to them. It should feel like an investment in their future.

Digital transformation is not just about acquiring new tools or signing multi-million dollar software licenses. It’s about how we choose to deploy capital across both technology and people. Too often, organizations pour their budgets into tools and platforms but overlook the human side of the equation: the psychological safety, mindset shifts, skill development and enablement required for adoption to succeed.

If employees are expected to work differently but are not supported in growing the capabilities to do so, transformation efforts fall short. The return on investment begins to diminish, not because the technology lacks potential, but because the people expected to use it haven’t been given the time, training, or confidence to integrate it meaningfully into their roles.

For transformation to truly take root and have the ability to generate exponential growth, a proportion of investment must be directed toward people through development programs, coaching, upskilling, and change enablement. This ensures employees feel equipped, empowered, and secure not only to perform in their roles with the new technologies, but to grow with them. When people and technology evolve in tandem, transformation becomes far more sustainable and impactful.

The truth is, digital transformation only works when everyone is on board. That includes not just leaders, but the employees whose work is changing the most. The most important stakeholder is not the CEO; it is the people doing the jobs that technology and AI are meant to support. When we ignore this, even the most advanced strategies fall flat.

Closing Thoughts

Digital transformation is not simply a race to adopt the latest technology or a nice-looking line on a strategy list. It is a profound journey, one that must be grounded in clear purpose, guided by intention, and centered on the people who make it real. Without this, even the most sophisticated tools and boldest ambitions risk falling short.

So, I ask again:
Why are you embarking on a journey of digital transformation?
What potential would it unlock?
What real problems for your team would it solve?
What better outcomes can your customers have?

If you can’t give a clear and defined answer yet, do not worry. That is where the real work begins. The true opportunity lies not in the technology itself, but in the clarity of why you transform and the genuine connection of your people to the purpose in the process.

When transformation is rooted in purpose and built with people, it becomes a source of momentum and trust, unlocking sustainable growth and meaningful change. This is how digital transformation moves from a buzzword to a business advantage, from disruption to opportunity.

Disclaimer: The insights shared in this article are based on personal reflections, independent analysis, and professional observations intended to illustrate broader themes in digital transformation and organizational needs. Examples referencing companies are drawn from publicly available sources and do not represent confidential or internal information. Additionally, any examples shared based on observations and research and may not reflect every individual’s experience. CultureHive is not affiliated with, endorsed by, or sponsored by the individuals or companies mentioned. Any opinions expressed are solely those of the author and do not reflect the official views or positions of the individuals or organizations referenced.